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NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

Holiday home with kitchen, steps from Duval Street

Photo gallery for NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

Front of the Home
Driveway
Front Steps
Living Area
Living Room

Reviews

10 out of 10, Loved by Guests
2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, Mallory Square
    ‪9 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪9 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Dining area

About this property

NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

Looking for the perfect spot to soak up some sunshine and unwind in Key West? You’ve found it. Island Pearls is a stylish and comfy 2-bedroom, 2-bath vacation rental located right on charming Fleming Street—just one block from all the action on Duval and directly across from the local favorite, Fausto's grocery store. You’ll be close to everything, so no need for a car (though there’s a driveway if you have one).

Step inside and you’ll feel instantly at home. The kitchen is modern and fully equipped, with sleek white finishes and custom cabinets that keep everything looking clean and polished. Whether you’re whipping up breakfast or sharing cocktails at the island, it’s a space that makes cooking and gathering easy and fun.

The living area is cozy yet modern, with hardwood floors, comfy seating, and just the right amount of Key West charm. Throw open the plantation shutters and let in that sweet Florida sunshine—it’s the perfect spot to kick back after a day of exploring.

Both bedrooms are en-suites, thoughtfully designed with comfy beds, soft linens, and fun, tropical wallpaper that’ll remind you you’re on island time. Each has its own private bathroom, making it great for couples, friends, or a small family traveling together.

Outside, the private pool and deck are where you’ll probably spend most of your time. Whether you’re sunbathing, taking a dip, or just enjoying the breeze with a drink in hand, it’s a peaceful spot that feels like your own slice of paradise.

Island Pearls is all about comfort, convenience, and that laid-back Key West vibe. It’s not just a place to stay—it’s a place to relax, recharge, and make some great memories.

Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know.

P.S. The pool is all yours—no sharing here!

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Key West

Located by the sea, this holiday home is in Key West Historic District, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Smathers Beach. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 1 min walk - 0.2 km
  • Harry S. Truman Little White House - 6 min walk - 0.5 km
  • Key West Aquarium - 7 min walk - 0.7 km
  • Mallory Square - 9 min walk - 0.8 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 14 min drive

Restaurants

  • ‪Margaritaville - ‬2 min walk
  • ‪Willie T's - ‬3 min walk
  • ‪Hard Rock Cafe - ‬5 min walk
  • ‪Kermit’s Key West Key Lime Shoppe - ‬3 min walk
  • ‪Jack Flats - ‬2 min walk

Frequently asked questions

Does NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool pet-friendly?

No, pets are not allowed at this property.

How much is parking at NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool?

On-site parking is available at the property.

What time is check-in at NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool?

Check-in begins at 4:00 PM.

What time is check-out at NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool?

Checkout is at 10:00 AM.

Where is NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool located?

Located in Key West Historic District, this holiday home is steps away from San Carlos Institute - Casa Cuba and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 42 out of 44 reviews
Rating 8 - Good. 2 out of 44 reviews
Rating 6 - Okay. 0 out of 44 reviews
Rating 4 - Poor. 0 out of 44 reviews
Rating 2 - Terrible. 0 out of 44 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

ginger p.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Island Pearl…wonderful, beautiful, perfect home
Stayed 3 nights in Dec 2025

10/10 Excellent

Kim W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect house for our stay in Key West. Exceptionally clean, open living area. The 2 bedrooms are on each side do the house, giving privacy. The private pool and tranquil backyard are added bonuses
Stayed 2 nights in Nov 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jim D.

Great place in perfect location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Had a wonderful time and the rental was like new and good location. Property mgr was easy to communicate with.

10/10 Excellent

priscilla b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house and pool. Clean, nicely decorated and comfortable. Perfect location to walk to everything. Would rent agin
Stayed 5 nights in Oct 2025

10/10 Excellent

michelle s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location nice place
Stayed 4 nights in Jul 2025

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
This unit was amazing!!! Appliances were very high quality. Unit was immaculate. Location was perfect - 2 blocks off Duval St., about 3/4 mile from the marina and less than a mile from Southernmost Point. Pool out back and a grocery store across the street. We plan to book this unit again!
Stayed 7 nights in Dec 2025

10/10 Excellent

Matthew M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
In the heart of everything...yet removed enough to enjoy our vacation. Rental is not the full house but the area you are granted access is fantastic (worked well for us). Home is well finished with two ensuites that worked perfectly for us, a beautiful kitchen and private pool. Comfortable and convienent, tough to beat.
Stayed 6 nights in Nov 2025

10/10 Excellent

Judy O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house, yard and pool and location. The communication with the rental staff was spot on and check in check out seamless.
Stayed 5 nights in Sep 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

David f.

location location location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Amazing location, luxury accommodations. Everything you needed is supplied. Fantastic communication and service. Very clean and comfortable. see you next year!!!

10/10 Excellent

Mike D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great updated house in the perfect location. Super easy communication with the host, who were very accommodating to our needs in the trip. Would definitely stay here again!
Stayed 3 nights in Aug 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Dan Y.

Fantastic gem in Old Town

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything about this rental was top notch. House seems recently renovated and rooms are tastefully decorated. Location is perfect as you can walk down either direction in Duval Street. Our little one loved the heated pool. Last but not least, Preferred Properties was very accommodating and super responsive!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Laura T.

Awesome Ley West House

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The place was beautiful and location superb!Perfect place to stay in Key West

10/10 Excellent

John H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Property

Outstanding location with beautiful features! Very comfortable!
Stayed 3 nights in Jul 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Randi D.

Wonderful!!!! Perfect house!!!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This house is perfect for 2 couples. The bedrooms and bathrooms are large. Kitchen has new appliances and the pool is beautiful! Perfect location to walk to attractions and restaurants. On a quiet street across from a grocery. Loved this house!!!!

10/10 Excellent

Stephanie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and customer service

We loved our location, the house and Key West!
Stayed 4 nights in Mar 2025

10/10 Excellent

Dianne T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful property

The house was beautiful, so comfortable and well thought out. Perfect location to all the action on Duval st, but out of the way enough to be quiet and peaceful. Would stay again in a heartbeat.
Stayed 2 nights in May 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Nancy T.

Great place to stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The home was beautifully decorated and a great location. We were able to walk to everything. There was even a grocery store across the street. The property management company was very helpful. I would definitely recommend staying at this beautiful home!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

David B.

Best Rental Property in Key West

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The house was modern with new appliances. The king size beds were comfortable. The walk in showers were spacious. The private pool was an oasis at the end of a busy day. And the location was perfect. Definitely staying here again.

10/10 Excellent

Julia C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect house and location!

The location was perfect! We walked everywhere! Very nice inside!
Stayed 3 nights in Apr 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Patti S.

Everything and More!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Not often are our expectations exceeded when renting a vacation home, but oh my goodness this place is the best. Two couples stayed comfortably. The location is fabulous, especially the grocery store across the street. Several area restaurants were all great. And the bookstore - well let's just say it became my new favorite place. The cherry on top was a dedicated parking space adjacent to the home. We would all give this location 10 stars if possible!

10/10 Excellent

James D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

key west

right off of Duval, central location, communication with manager was prompt and fast..
Stayed 3 nights in Apr 2025

10/10 Excellent

Eric S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Place

Place was perfect and property management was great. Will definitely try to stay here again.
Stayed 3 nights in Aug 2024

10/10 Excellent

William

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome place to stay!

Really convenient location, close to everything! Very clean and well appointed. Beds and linens were fantastic. The backyard pool is a nice touch on hot days. Upstairs long term residents are phenomenal, treated us like family and provided tons of tips only locals would know. One of the better trips we have made to key west and this location had a lot to do with the experience. We would certainly book here again!
Stayed 4 nights in May 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Gina W.

Great house in great location!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved the house. It was clean, well maintained, and in a great location! We loved having the grocery store across the street and walked or rode bikes to everything!

10/10 Excellent

jean-michel d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Inside is a 5*

First i have been impressed by the professionalism of the property manager ! When we arrive we are doubting because outside needs improvement… but when we open the door whoaa ! newly refurbished, with taste and confort .. A wonderful place to stay , the pool is a us … when the outside will be refurbished this place will be a all star !
Stayed 2 nights in Jul 2025

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